Methanol → HCID 58575609, compound

HRID 1807845Notes

Reaction equation

HRID 1807845 reaction equation
[NH2:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:15][O:16][CH3:17])[CH:3]=1.[Cl-].[NH4+].O1CCCC1.CO>O>[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:15][O:16][CH3:17])[CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 58575185HCID 58575185, compound

Product 1

HCID 58575609HCID 58575609, compoundYield 105.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a mixed liquid of 4.70 g of methyl 4-amino-2-(methoxymethyl)-5-nitrobenzoate, 750 mg of ammonium chloride, 47.0 mL of tetrahydrofuran, 94.0 mL of methanol, and 14.0 mL of water was added 7.65 g of reduced iron, followed by stirring at 80° C. overnight. After cooling to room temperature, the insoluble materials were filtered through celite and the filtrate was evaporated under reduced pressure to obtain 4.33 g of methyl 4,5-diamino-2-(methoxymethyl)benzoate as a brown solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe insoluble materials were filtered through celite
  3. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9e4fd4cd861f47b69609ddade59c5b3e
Source dataset
uspto-grants-2013_01
Patent number
US08357688B2

Reaction notes

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